# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_avk14f5
_database_code_depnum_ccdc_archive 'CCDC 1888875'
loop_
_audit_author_name
_audit_author_address
'Boris Averkiev'
;New Mexico Highlands University
United States of America
;
_audit_update_record             
;
2019-01-08 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;
_audit_creation_date             2018-07-27
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        3-phenylpyrrolidine-2,5-dione
_chemical_formula_moiety         'C10 H9 N O2'
_chemical_formula_sum            'C10 H9 N O2'
_chemical_formula_weight         175.18
_chemical_melting_point          349.8

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.285(5)
_cell_length_b                   10.118(5)
_cell_length_c                   15.913(8)
_cell_angle_alpha                80.568(6)
_cell_angle_beta                 81.516(6)
_cell_angle_gamma                65.604(6)
_cell_volume                     1337.8(11)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    5654
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.30
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1104 before and 0.0440 after correction.
The Ratio of minimum to maximum transmission is 0.8583.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19911
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.722
_diffrn_reflns_theta_min         2.225
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5607
_reflns_number_total             8123
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXL (Sheldrick, 2008)'
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         8123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²+0.1977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1299
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.34061(13) 0.62623(14) 0.23887(7) 0.0511(3) Uani 1 1 d . . . . .
O2A O 0.69983(11) 0.43005(11) 0.01898(6) 0.0341(2) Uani 1 1 d . . . . .
N1A N 0.49645(13) 0.53849(12) 0.11771(7) 0.0283(2) Uani 1 1 d . . . . .
H1A H 0.419(2) 0.561(2) 0.0832(13) 0.058(5) Uiso 1 1 d . . . . .
C1A C 0.47074(16) 0.56944(14) 0.20241(9) 0.0315(3) Uani 1 1 d . . . . .
C2A C 0.63304(16) 0.52409(14) 0.23429(8) 0.0286(3) Uani 1 1 d . . . . .
H2A H 0.6470(18) 0.6144(17) 0.2290(10) 0.034(4) Uiso 1 1 d . . . . .
C3A C 0.74856(15) 0.43213(15) 0.16572(8) 0.0292(3) Uani 1 1 d . . . . .
H3AA H 0.7824(19) 0.3264(18) 0.1852(10) 0.037(4) Uiso 1 1 d . . . . .
H3AB H 0.838(2) 0.4542(19) 0.1483(11) 0.047(5) Uiso 1 1 d . . . . .
C4A C 0.65182(15) 0.46357(13) 0.09180(8) 0.0255(2) Uani 1 1 d . . . . .
C5A C 0.64838(15) 0.45236(14) 0.32567(8) 0.0292(3) Uani 1 1 d . . . . .
C6A C 0.68269(16) 0.51717(15) 0.38609(9) 0.0332(3) Uani 1 1 d . . . . .
H6A H 0.6897(19) 0.6123(18) 0.3707(10) 0.041(4) Uiso 1 1 d . . . . .
C7A C 0.70120(18) 0.45064(18) 0.46981(10) 0.0414(3) Uani 1 1 d . . . . .
H7A H 0.722(2) 0.500(2) 0.5123(12) 0.054(5) Uiso 1 1 d . . . . .
C8A C 0.68719(19) 0.31884(19) 0.49310(10) 0.0465(4) Uani 1 1 d . . . . .
H8A H 0.697(2) 0.276(2) 0.5532(13) 0.056(5) Uiso 1 1 d . . . . .
C9A C 0.6540(2) 0.25295(19) 0.43337(11) 0.0486(4) Uani 1 1 d . . . . .
H9A H 0.643(2) 0.157(2) 0.4471(13) 0.067(6) Uiso 1 1 d . . . . .
C10A C 0.6334(2) 0.31938(17) 0.34968(10) 0.0410(3) Uani 1 1 d . . . . .
H10A H 0.608(2) 0.269(2) 0.3050(12) 0.056(5) Uiso 1 1 d . . . . .
O1B O 1.04658(13) 0.37878(11) -0.15909(7) 0.0417(3) Uani 1 1 d . . . . .
O2B O 0.83447(11) 0.05003(11) -0.04382(6) 0.0361(2) Uani 1 1 d . . . . .
N1B N 0.93033(13) 0.22863(12) -0.08544(7) 0.0280(2) Uani 1 1 d . . . . .
H1B H 0.8676(19) 0.2889(18) -0.0490(10) 0.035(4) Uiso 1 1 d . . . . .
C1B C 1.03721(15) 0.26126(14) -0.14650(8) 0.0279(3) Uani 1 1 d . . . . .
C2B C 1.13773(14) 0.12375(13) -0.18926(8) 0.0263(2) Uani 1 1 d . . . . .
H2B H 1.2392(18) 0.0818(16) -0.1590(9) 0.031(4) Uiso 1 1 d . . . . .
C3B C 1.04640(17) 0.02423(15) -0.15988(9) 0.0311(3) Uani 1 1 d . . . . .
H3BA H 1.118(2) -0.077(2) -0.1362(11) 0.051(5) Uiso 1 1 d . . . . .
H3BB H 0.9902(19) 0.0209(17) -0.2050(11) 0.040(4) Uiso 1 1 d . . . . .
C4B C 0.92512(14) 0.09676(14) -0.08965(8) 0.0267(3) Uani 1 1 d . . . . .
C5B C 1.17641(15) 0.14984(14) -0.28467(8) 0.0286(3) Uani 1 1 d . . . . .
C6B C 1.33251(16) 0.08483(15) -0.31973(9) 0.0324(3) Uani 1 1 d . . . . .
H6B H 1.4135(19) 0.0245(17) -0.2818(10) 0.034(4) Uiso 1 1 d . . . . .
C7B C 1.37176(19) 0.10546(17) -0.40717(10) 0.0396(3) Uani 1 1 d . . . . .
H7B H 1.486(2) 0.0583(19) -0.4312(11) 0.048(5) Uiso 1 1 d . . . . .
C8B C 1.2552(2) 0.19022(19) -0.46062(10) 0.0443(4) Uani 1 1 d . . . . .
H8B H 1.283(2) 0.2087(19) -0.5216(12) 0.051(5) Uiso 1 1 d . . . . .
C9B C 1.0991(2) 0.2550(2) -0.42636(11) 0.0510(4) Uani 1 1 d . . . . .
H9B H 1.015(3) 0.321(2) -0.4600(13) 0.067(6) Uiso 1 1 d . . . . .
C10B C 1.05959(18) 0.23583(19) -0.33884(10) 0.0433(4) Uani 1 1 d . . . . .
H10B H 0.950(2) 0.2865(19) -0.3161(11) 0.047(5) Uiso 1 1 d . . . . .
O1C O 0.55806(11) 0.20935(11) 0.16533(6) 0.0353(2) Uani 1 1 d . . . . .
O2C O 0.39810(13) 0.17567(13) -0.08457(7) 0.0456(3) Uani 1 1 d . . . . .
N1C N 0.50971(13) 0.18303(12) 0.03318(7) 0.0283(2) Uani 1 1 d . . . . .
H1C H 0.614(2) 0.146(2) 0.0129(12) 0.055(5) Uiso 1 1 d . . . . .
C1C C 0.46577(14) 0.21915(13) 0.11549(8) 0.0262(2) Uani 1 1 d . . . . .
C2C C 0.28483(14) 0.27477(13) 0.13129(8) 0.0268(3) Uani 1 1 d . . . . .
H2C H 0.2426(17) 0.3793(16) 0.1389(9) 0.027(4) Uiso 1 1 d . . . . .
C3C C 0.23401(16) 0.25540(16) 0.04771(9) 0.0309(3) Uani 1 1 d . . . . .
H3CA H 0.161(2) 0.3464(18) 0.0212(10) 0.040(4) Uiso 1 1 d . . . . .
H3CB H 0.191(2) 0.1818(19) 0.0557(10) 0.043(4) Uiso 1 1 d . . . . .
C4C C 0.38412(16) 0.20095(14) -0.01099(8) 0.0297(3) Uani 1 1 d . . . . .
C5C C 0.23268(14) 0.19625(14) 0.21159(8) 0.0262(2) Uani 1 1 d . . . . .
C6C C 0.12115(16) 0.27488(16) 0.27336(9) 0.0358(3) Uani 1 1 d . . . . .
H6C H 0.0834(19) 0.3823(19) 0.2656(10) 0.041(4) Uiso 1 1 d . . . . .
C7C C 0.06967(18) 0.20200(19) 0.34539(10) 0.0444(4) Uani 1 1 d . . . . .
H7C H -0.009(2) 0.257(2) 0.3893(12) 0.056(5) Uiso 1 1 d . . . . .
C8C C 0.13035(18) 0.05123(19) 0.35736(10) 0.0426(4) Uani 1 1 d . . . . .
H8C H 0.093(2) -0.0001(19) 0.4100(12) 0.050(5) Uiso 1 1 d . . . . .
C9C C 0.24255(18) -0.02811(17) 0.29681(9) 0.0373(3) Uani 1 1 d . . . . .
H9C H 0.284(2) -0.136(2) 0.3059(11) 0.048(5) Uiso 1 1 d . . . . .
C10C C 0.29224(16) 0.04418(14) 0.22382(9) 0.0305(3) Uani 1 1 d . . . . .
H10C H 0.3703(19) -0.0118(17) 0.1804(10) 0.036(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C1A 1.2065(17) . ?
O2A C4A 1.2280(16) . ?
N1A H1A 0.90(2) . ?
N1A C1A 1.3976(18) . ?
N1A C4A 1.3599(17) . ?
C1A C2A 1.522(2) . ?
C2A H2A 0.964(16) . ?
C2A C3A 1.5394(19) . ?
C2A C5A 1.5137(19) . ?
C3A H3AA 0.991(16) . ?
C3A H3AB 0.935(18) . ?
C3A C4A 1.4983(19) . ?
C5A C6A 1.3876(19) . ?
C5A C10A 1.395(2) . ?
C6A H6A 0.980(17) . ?
C6A C7A 1.391(2) . ?
C7A H7A 0.986(19) . ?
C7A C8A 1.378(3) . ?
C8A H8A 0.98(2) . ?
C8A C9A 1.381(3) . ?
C9A H9A 1.00(2) . ?
C9A C10A 1.392(2) . ?
C10A H10A 1.045(19) . ?
O1B C1B 1.2099(16) . ?
O2B C4B 1.2241(16) . ?
N1B H1B 0.878(16) . ?
N1B C1B 1.3852(17) . ?
N1B C4B 1.3677(18) . ?
C1B C2B 1.5232(19) . ?
C2B H2B 1.018(15) . ?
C2B C3B 1.5445(18) . ?
C2B C5B 1.5132(19) . ?
C3B H3BA 1.011(19) . ?
C3B H3BB 0.959(17) . ?
C3B C4B 1.5069(19) . ?
C5B C6B 1.3924(19) . ?
C5B C10B 1.388(2) . ?
C6B H6B 0.968(16) . ?
C6B C7B 1.389(2) . ?
C7B H7B 1.010(18) . ?
C7B C8B 1.377(2) . ?
C8B H8B 0.975(18) . ?
C8B C9B 1.387(3) . ?
C9B H9B 0.96(2) . ?
C9B C10B 1.390(2) . ?
C10B H10B 0.973(18) . ?
O1C C1C 1.2156(16) . ?
O2C C4C 1.2161(17) . ?
N1C H1C 0.910(19) . ?
N1C C1C 1.3754(18) . ?
N1C C4C 1.3828(18) . ?
C1C C2C 1.5307(19) . ?
C2C H2C 0.986(15) . ?
C2C C3C 1.542(2) . ?
C2C C5C 1.5170(18) . ?
C3C H3CA 0.962(17) . ?
C3C H3CB 0.964(18) . ?
C3C C4C 1.506(2) . ?
C5C C6C 1.3953(19) . ?
C5C C10C 1.3936(19) . ?
C6C H6C 0.986(17) . ?
C6C C7C 1.392(2) . ?
C7C H7C 0.984(19) . ?
C7C C8C 1.381(2) . ?
C8C H8C 1.006(18) . ?
C8C C9C 1.387(2) . ?
C9C H9C 0.986(18) . ?
C9C C10C 1.393(2) . ?
C10C H10C 0.983(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A H1A 124.6(13) . . ?
C4A N1A H1A 121.6(13) . . ?
C4A N1A C1A 113.68(11) . . ?
O1A C1A N1A 123.62(13) . . ?
O1A C1A C2A 129.19(13) . . ?
N1A C1A C2A 107.14(11) . . ?
C1A C2A H2A 103.9(9) . . ?
C1A C2A C3A 103.56(11) . . ?
C3A C2A H2A 107.6(9) . . ?
C5A C2A C1A 114.93(11) . . ?
C5A C2A H2A 110.0(9) . . ?
C5A C2A C3A 115.95(11) . . ?
C2A C3A H3AA 110.8(9) . . ?
C2A C3A H3AB 114.1(11) . . ?
H3AA C3A H3AB 110.0(14) . . ?
C4A C3A C2A 104.85(11) . . ?
C4A C3A H3AA 106.5(9) . . ?
C4A C3A H3AB 110.2(11) . . ?
O2A C4A N1A 123.82(12) . . ?
O2A C4A C3A 127.52(12) . . ?
N1A C4A C3A 108.67(11) . . ?
C6A C5A C2A 119.71(12) . . ?
C6A C5A C10A 119.28(13) . . ?
C10A C5A C2A 120.97(12) . . ?
C5A C6A H6A 120.2(10) . . ?
C5A C6A C7A 120.38(14) . . ?
C7A C6A H6A 119.4(10) . . ?
C6A C7A H7A 119.2(11) . . ?
C8A C7A C6A 120.12(15) . . ?
C8A C7A H7A 120.6(11) . . ?
C7A C8A H8A 118.1(11) . . ?
C7A C8A C9A 119.99(15) . . ?
C9A C8A H8A 121.9(11) . . ?
C8A C9A H9A 123.0(12) . . ?
C8A C9A C10A 120.37(16) . . ?
C10A C9A H9A 116.7(12) . . ?
C5A C10A H10A 120.3(10) . . ?
C9A C10A C5A 119.85(15) . . ?
C9A C10A H10A 119.9(10) . . ?
C1B N1B H1B 123.3(10) . . ?
C4B N1B H1B 122.6(10) . . ?
C4B N1B C1B 114.02(11) . . ?
O1B C1B N1B 123.74(12) . . ?
O1B C1B C2B 128.68(12) . . ?
N1B C1B C2B 107.55(11) . . ?
C1B C2B H2B 102.9(8) . . ?
C1B C2B C3B 103.41(10) . . ?
C3B C2B H2B 108.5(8) . . ?
C5B C2B C1B 114.83(11) . . ?
C5B C2B H2B 109.9(8) . . ?
C5B C2B C3B 116.33(11) . . ?
C2B C3B H3BA 112.3(10) . . ?
C2B C3B H3BB 111.3(10) . . ?
H3BA C3B H3BB 111.1(14) . . ?
C4B C3B C2B 105.04(11) . . ?
C4B C3B H3BA 109.0(10) . . ?
C4B C3B H3BB 107.8(10) . . ?
O2B C4B N1B 124.36(12) . . ?
O2B C4B C3B 127.46(12) . . ?
N1B C4B C3B 108.17(11) . . ?
C6B C5B C2B 119.57(12) . . ?
C10B C5B C2B 121.68(12) . . ?
C10B C5B C6B 118.74(13) . . ?
C5B C6B H6B 118.5(9) . . ?
C7B C6B C5B 121.00(13) . . ?
C7B C6B H6B 120.5(9) . . ?
C6B C7B H7B 119.8(10) . . ?
C8B C7B C6B 119.96(14) . . ?
C8B C7B H7B 120.3(10) . . ?
C7B C8B H8B 119.9(11) . . ?
C7B C8B C9B 119.48(15) . . ?
C9B C8B H8B 120.5(11) . . ?
C8B C9B H9B 122.9(12) . . ?
C8B C9B C10B 120.75(15) . . ?
C10B C9B H9B 116.2(12) . . ?
C5B C10B C9B 120.06(15) . . ?
C5B C10B H10B 120.8(10) . . ?
C9B C10B H10B 119.1(10) . . ?
C1C N1C H1C 120.8(12) . . ?
C1C N1C C4C 113.93(11) . . ?
C4C N1C H1C 125.2(12) . . ?
O1C C1C N1C 124.34(12) . . ?
O1C C1C C2C 127.15(12) . . ?
N1C C1C C2C 108.50(10) . . ?
C1C C2C H2C 108.2(8) . . ?
C1C C2C C3C 103.62(10) . . ?
C3C C2C H2C 110.1(8) . . ?
C5C C2C C1C 112.18(10) . . ?
C5C C2C H2C 107.7(8) . . ?
C5C C2C C3C 114.86(11) . . ?
C2C C3C H3CA 111.8(10) . . ?
C2C C3C H3CB 112.6(10) . . ?
H3CA C3C H3CB 110.9(14) . . ?
C4C C3C C2C 105.72(11) . . ?
C4C C3C H3CA 108.8(10) . . ?
C4C C3C H3CB 106.7(10) . . ?
O2C C4C N1C 124.02(13) . . ?
O2C C4C C3C 127.89(13) . . ?
N1C C4C C3C 108.09(12) . . ?
C6C C5C C2C 120.66(12) . . ?
C10C C5C C2C 120.49(11) . . ?
C10C C5C C6C 118.83(12) . . ?
C5C C6C H6C 118.3(9) . . ?
C7C C6C C5C 120.28(14) . . ?
C7C C6C H6C 121.3(9) . . ?
C6C C7C H7C 120.8(11) . . ?
C8C C7C C6C 120.50(14) . . ?
C8C C7C H7C 118.7(11) . . ?
C7C C8C H8C 119.7(10) . . ?
C7C C8C C9C 119.72(14) . . ?
C9C C8C H8C 120.6(10) . . ?
C8C C9C H9C 118.7(10) . . ?
C8C C9C C10C 120.05(14) . . ?
C10C C9C H9C 121.2(10) . . ?
C5C C10C H10C 119.2(9) . . ?
C9C C10C C5C 120.60(13) . . ?
C9C C10C H10C 120.2(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O2A 0.90(2) 2.07(2) 2.9355(19) 162.1(18) 2_665 yes
N1B H1B O2A 0.878(16) 1.951(17) 2.8201(17) 170.1(15) . yes
N1C H1C O2B 0.910(19) 2.012(19) 2.9159(19) 171.7(18) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A C1A C2A C3A 169.20(15) . . . . ?
O1A C1A C2A C5A 41.7(2) . . . . ?
N1A C1A C2A C3A -13.15(13) . . . . ?
N1A C1A C2A C5A -140.63(12) . . . . ?
C1A N1A C4A O2A -177.54(12) . . . . ?
C1A N1A C4A C3A 2.16(15) . . . . ?
C1A C2A C3A C4A 14.02(13) . . . . ?
C1A C2A C5A C6A -118.48(13) . . . . ?
C1A C2A C5A C10A 63.51(17) . . . . ?
C2A C3A C4A O2A 169.19(12) . . . . ?
C2A C3A C4A N1A -10.49(13) . . . . ?
C2A C5A C6A C7A -178.34(13) . . . . ?
C2A C5A C10A C9A 177.56(14) . . . . ?
C3A C2A C5A C6A 120.60(14) . . . . ?
C3A C2A C5A C10A -57.41(18) . . . . ?
C4A N1A C1A O1A -174.86(13) . . . . ?
C4A N1A C1A C2A 7.32(15) . . . . ?
C5A C2A C3A C4A 140.86(11) . . . . ?
C5A C6A C7A C8A 0.7(2) . . . . ?
C6A C5A C10A C9A -0.5(2) . . . . ?
C6A C7A C8A C9A -0.3(2) . . . . ?
C7A C8A C9A C10A -0.4(3) . . . . ?
C8A C9A C10A C5A 0.8(3) . . . . ?
C10A C5A C6A C7A -0.3(2) . . . . ?
O1B C1B C2B C3B -168.64(14) . . . . ?
O1B C1B C2B C5B -40.85(18) . . . . ?
N1B C1B C2B C3B 13.36(13) . . . . ?
N1B C1B C2B C5B 141.15(11) . . . . ?
C1B N1B C4B O2B -177.00(12) . . . . ?
C1B N1B C4B C3B 2.19(15) . . . . ?
C1B C2B C3B C4B -11.81(13) . . . . ?
C1B C2B C5B C6B 131.07(13) . . . . ?
C1B C2B C5B C10B -49.80(17) . . . . ?
C2B C3B C4B O2B -174.26(13) . . . . ?
C2B C3B C4B N1B 6.57(14) . . . . ?
C2B C5B C6B C7B 179.39(12) . . . . ?
C2B C5B C10B C9B -178.71(15) . . . . ?
C3B C2B C5B C6B -107.99(14) . . . . ?
C3B C2B C5B C10B 71.14(17) . . . . ?
C4B N1B C1B O1B 171.66(12) . . . . ?
C4B N1B C1B C2B -10.22(14) . . . . ?
C5B C2B C3B C4B -138.66(11) . . . . ?
C5B C6B C7B C8B -0.6(2) . . . . ?
C6B C5B C10B C9B 0.4(2) . . . . ?
C6B C7B C8B C9B 0.3(2) . . . . ?
C7B C8B C9B C10B 0.4(3) . . . . ?
C8B C9B C10B C5B -0.7(3) . . . . ?
C10B C5B C6B C7B 0.2(2) . . . . ?
O1C C1C C2C C3C -177.56(12) . . . . ?
O1C C1C C2C C5C -53.09(17) . . . . ?
N1C C1C C2C C3C 3.51(12) . . . . ?
N1C C1C C2C C5C 127.98(11) . . . . ?
C1C N1C C4C O2C 179.64(12) . . . . ?
C1C N1C C4C C3C -0.38(14) . . . . ?
C1C C2C C3C C4C -3.61(13) . . . . ?
C1C C2C C5C C6C 129.06(13) . . . . ?
C1C C2C C5C C10C -52.69(16) . . . . ?
C2C C3C C4C O2C -177.40(13) . . . . ?
C2C C3C C4C N1C 2.62(14) . . . . ?
C2C C5C C6C C7C 177.67(13) . . . . ?
C2C C5C C10C C9C -178.92(12) . . . . ?
C3C C2C C5C C6C -112.96(14) . . . . ?
C3C C2C C5C C10C 65.29(15) . . . . ?
C4C N1C C1C O1C 178.96(11) . . . . ?
C4C N1C C1C C2C -2.08(14) . . . . ?
C5C C2C C3C C4C -126.32(11) . . . . ?
C5C C6C C7C C8C 1.2(2) . . . . ?
C6C C5C C10C C9C -0.6(2) . . . . ?
C6C C7C C8C C9C -0.5(2) . . . . ?
C7C C8C C9C C10C -0.8(2) . . . . ?
C8C C9C C10C C5C 1.3(2) . . . . ?
C10C C5C C6C C7C -0.6(2) . . . . ?

_olex2_submission_original_sample_id AVK14F5
_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_PII_100K
_database_code_depnum_ccdc_archive 'CCDC 1957488'
loop_
_audit_author_name
_audit_author_address
'Tatiana Timofeeva'
;New Mexico Highlands University
United States of America
;
_audit_update_record             
;
2019-10-03 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;
_audit_creation_date             2019-09-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        rac-3-phenylpyrrolidin-2,5-dione
_chemical_formula_moiety         'C10 H9 N O2'
_chemical_formula_sum            'C10 H9 N O2'
_chemical_formula_weight         175.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.51(14)
_cell_length_b                   5.64(5)
_cell_length_c                   20.49(16)
_cell_angle_alpha                90
_cell_angle_beta                 108.10(10)
_cell_angle_gamma                90
_cell_volume                     1704(25)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    383
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      17.581
_cell_measurement_theta_min      3.756
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_correction_T_min  0.3098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1340 before and 0.0496 after correction. The Ratio of minimum to maximum transmission is 0.4163. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1999
_diffrn_reflns_av_unetI/netI     0.1558
_diffrn_reflns_Laue_measured_fraction_full 0.934
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2613
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        17.869
_diffrn_reflns_theta_max         17.869
_diffrn_reflns_theta_min         2.091
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                473
_reflns_number_total             1071
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.866
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         1071
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1352
_refine_ls_R_factor_gt           0.0691
_refine_ls_restrained_S_all      0.866
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0696P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1687
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C3A(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C2A(H2AA,H2AB)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N1A(H1A), C6(H6), C10A(H10A), C7(H7), C9A(H9A), C8(H8), C8A(H8A),
 C9(H9), C7A(H7A), C10(H10), C6A(H6A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.3392(7) 0.1477(17) 0.6173(4) 0.072(3) Uani 1 1 d . . . . .
O2A O 0.6087(5) 0.3625(14) 0.6567(4) 0.060(3) Uani 1 1 d . . . . .
O1 O 0.5731(7) -0.1739(17) 0.5589(4) 0.069(3) Uani 1 1 d . . . . .
O1A O 0.5860(7) 1.0246(14) 0.7715(3) 0.059(3) Uani 1 1 d . . . . .
N1 N 0.4677(10) 0.0173(18) 0.5987(4) 0.051(3) Uani 1 1 d . . . . .
H1 H 0.502560 0.132201 0.621472 0.061 Uiso 1 1 calc R . . . .
N1A N 0.5833(7) 0.668(2) 0.7189(5) 0.042(3) Uani 1 1 d . . . . .
H1A H 0.529784 0.622052 0.720752 0.051 Uiso 1 1 calc R . . . .
C4 C 0.3818(13) 0.000(3) 0.5972(6) 0.059(5) Uani 1 1 d . . . . .
C4A C 0.6345(11) 0.540(3) 0.6887(7) 0.053(4) Uani 1 1 d . . . . .
C1 C 0.5011(11) -0.152(3) 0.5630(7) 0.052(4) Uani 1 1 d . . . . .
C1A C 0.6247(10) 0.877(3) 0.7464(6) 0.047(4) Uani 1 1 d . . . . .
C2 C 0.4167(10) -0.3130(19) 0.5321(6) 0.060(4) Uani 1 1 d . . . . .
H2A H 0.393125 -0.293581 0.481584 0.072 Uiso 1 1 calc R . . . .
H2B H 0.432617 -0.481584 0.542649 0.072 Uiso 1 1 calc R . . . .
C2A C 0.7122(11) 0.8916(18) 0.7350(6) 0.066(4) Uani 1 1 d . . . . .
H2AA H 0.761060 0.908038 0.779312 0.079 Uiso 1 1 calc R . . . .
H2AB H 0.714082 1.030819 0.706083 0.079 Uiso 1 1 calc R . . . .
C3 C 0.3477(10) -0.234(2) 0.5648(6) 0.054(4) Uani 1 1 d . . . . .
H3 H 0.352770 -0.346325 0.603574 0.065 Uiso 1 1 calc R . . . .
C3A C 0.7248(9) 0.664(2) 0.6990(5) 0.045(3) Uani 1 1 d . . . . .
H3A H 0.730800 0.704479 0.653056 0.053 Uiso 1 1 calc R . . . .
C5 C 0.2489(9) -0.237(3) 0.5214(6) 0.046(4) Uani 1 1 d . . . . .
C5A C 0.8020(9) 0.510(2) 0.7367(9) 0.044(4) Uani 1 1 d . . . . .
C6 C 0.1942(14) -0.419(2) 0.5208(6) 0.059(4) Uani 1 1 d . . . . .
H6 H 0.217066 -0.552438 0.549256 0.071 Uiso 1 1 calc R . . . .
C10A C 0.8497(13) 0.383(3) 0.7060(6) 0.062(4) Uani 1 1 d . . . . .
H10A H 0.834697 0.396075 0.657542 0.075 Uiso 1 1 calc R . . . .
C7 C 0.1045(14) -0.418(3) 0.4796(8) 0.083(5) Uani 1 1 d . . . . .
H7 H 0.066315 -0.549522 0.479616 0.100 Uiso 1 1 calc R . . . .
C9A C 0.9194(10) 0.231(2) 0.7390(10) 0.066(4) Uani 1 1 d . . . . .
H9A H 0.953236 0.149753 0.714442 0.079 Uiso 1 1 calc R . . . .
C8 C 0.0722(9) -0.230(4) 0.4396(7) 0.068(4) Uani 1 1 d . . . . .
H8 H 0.010071 -0.223743 0.412717 0.081 Uiso 1 1 calc R . . . .
C8A C 0.9378(10) 0.204(2) 0.8070(10) 0.062(4) Uani 1 1 d . . . . .
H8A H 0.985738 0.102527 0.831945 0.075 Uiso 1 1 calc R . . . .
C9 C 0.1295(17) -0.049(2) 0.4381(7) 0.088(6) Uani 1 1 d . . . . .
H9 H 0.107635 0.081936 0.408232 0.106 Uiso 1 1 calc R . . . .
C7A C 0.8872(13) 0.322(3) 0.8393(6) 0.063(4) Uani 1 1 d . . . . .
H7A H 0.900153 0.298618 0.887352 0.075 Uiso 1 1 calc R . . . .
C10 C 0.2177(12) -0.052(3) 0.4787(8) 0.084(5) Uani 1 1 d . . . . .
H10 H 0.257104 0.075694 0.476967 0.101 Uiso 1 1 calc R . . . .
C6A C 0.8177(10) 0.474(2) 0.8066(9) 0.059(4) Uani 1 1 d . . . . .
H6A H 0.782079 0.550118 0.830605 0.071 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C4 1.214(17) . ?
O2A C4A 1.197(15) . ?
O1 C1 1.153(18) . ?
O1A C1A 1.229(16) . ?
N1 H1 0.8800 . ?
N1 C4 1.33(2) . ?
N1 C1 1.395(18) . ?
N1A H1A 0.8800 . ?
N1A C4A 1.355(16) . ?
N1A C1A 1.379(17) . ?
C4 C3 1.50(2) . ?
C4A C3A 1.52(2) . ?
C1 C2 1.56(2) . ?
C1A C2A 1.45(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.497(19) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.524(16) . ?
C3 H3 1.0000 . ?
C3 C5 1.514(19) . ?
C3A H3A 1.0000 . ?
C3A C5A 1.486(17) . ?
C5 C6 1.333(16) . ?
C5 C10 1.352(16) . ?
C5A C10A 1.323(17) . ?
C5A C6A 1.391(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.38(2) . ?
C10A H10A 0.9500 . ?
C10A C9A 1.379(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.337(16) . ?
C9A H9A 0.9500 . ?
C9A C8A 1.342(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.365(19) . ?
C8A H8A 0.9500 . ?
C8A C7A 1.351(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.36(2) . ?
C7A H7A 0.9500 . ?
C7A C6A 1.378(16) . ?
C10 H10 0.9500 . ?
C6A H6A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 H1 121.0 . . ?
C4 N1 C1 118.0(14) . . ?
C1 N1 H1 121.0 . . ?
C4A N1A H1A 124.0 . . ?
C4A N1A C1A 112.1(14) . . ?
C1A N1A H1A 124.0 . . ?
O2 C4 N1 126.1(16) . . ?
O2 C4 C3 127.1(18) . . ?
N1 C4 C3 106.8(14) . . ?
O2A C4A N1A 123.5(16) . . ?
O2A C4A C3A 126.7(15) . . ?
N1A C4A C3A 109.8(13) . . ?
O1 C1 N1 129.6(16) . . ?
O1 C1 C2 128.1(15) . . ?
N1 C1 C2 102.2(14) . . ?
O1A C1A N1A 121.7(16) . . ?
O1A C1A C2A 129.2(15) . . ?
N1A C1A C2A 108.9(13) . . ?
C1 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
C3 C2 C1 105.7(12) . . ?
C3 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
C1A C2A H2AA 110.3 . . ?
C1A C2A H2AB 110.3 . . ?
C1A C2A C3A 107.3(11) . . ?
H2AA C2A H2AB 108.5 . . ?
C3A C2A H2AA 110.3 . . ?
C3A C2A H2AB 110.3 . . ?
C4 C3 C2 105.0(13) . . ?
C4 C3 H3 106.0 . . ?
C4 C3 C5 115.0(13) . . ?
C2 C3 H3 106.0 . . ?
C2 C3 C5 117.8(13) . . ?
C5 C3 H3 106.0 . . ?
C4A C3A C2A 101.7(11) . . ?
C4A C3A H3A 109.1 . . ?
C2A C3A H3A 109.1 . . ?
C5A C3A C4A 111.2(12) . . ?
C5A C3A C2A 116.3(11) . . ?
C5A C3A H3A 109.1 . . ?
C6 C5 C3 122.5(16) . . ?
C6 C5 C10 119.5(13) . . ?
C10 C5 C3 117.8(16) . . ?
C10A C5A C3A 123.3(17) . . ?
C10A C5A C6A 117.6(12) . . ?
C6A C5A C3A 118.5(16) . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(12) . . ?
C7 C6 H6 119.4 . . ?
C5A C10A H10A 117.5 . . ?
C5A C10A C9A 125.0(13) . . ?
C9A C10A H10A 117.5 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.5(13) . . ?
C8 C7 H7 120.2 . . ?
C10A C9A H9A 121.2 . . ?
C8A C9A C10A 117.5(12) . . ?
C8A C9A H9A 121.2 . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.1(14) . . ?
C9 C8 H8 120.5 . . ?
C9A C8A H8A 120.5 . . ?
C9A C8A C7A 118.9(13) . . ?
C7A C8A H8A 120.5 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(13) . . ?
C10 C9 H9 119.5 . . ?
C8A C7A H7A 118.2 . . ?
C8A C7A C6A 123.6(13) . . ?
C6A C7A H7A 118.2 . . ?
C5 C10 C9 119.6(14) . . ?
C5 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C5A C6A H6A 121.5 . . ?
C7A C6A C5A 117.0(12) . . ?
C7A C6A H6A 121.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O1A 0.88 1.93 2.81(3) 177.8 2_646 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C4 C3 C2 164.1(12) . . . . ?
O2 C4 C3 C5 33.0(19) . . . . ?
O2A C4A C3A C2A 172.7(10) . . . . ?
O2A C4A C3A C5A -62.8(15) . . . . ?
O1 C1 C2 C3 168.4(13) . . . . ?
O1A C1A C2A C3A -177.0(10) . . . . ?
N1 C4 C3 C2 -14.6(12) . . . . ?
N1 C4 C3 C5 -145.7(12) . . . . ?
N1 C1 C2 C3 -9.2(11) . . . . ?
N1A C4A C3A C2A -4.3(11) . . . . ?
N1A C4A C3A C5A 120.2(12) . . . . ?
N1A C1A C2A C3A -1.9(11) . . . . ?
C4 N1 C1 O1 -177.6(13) . . . . ?
C4 N1 C1 C2 -0.1(12) . . . . ?
C4 C3 C5 C6 -141.0(12) . . . . ?
C4 C3 C5 C10 43.2(17) . . . . ?
C4A N1A C1A O1A 174.6(10) . . . . ?
C4A N1A C1A C2A -1.0(11) . . . . ?
C4A C3A C5A C10A 98.2(15) . . . . ?
C4A C3A C5A C6A -72.9(14) . . . . ?
C1 N1 C4 O2 -169.3(11) . . . . ?
C1 N1 C4 C3 9.4(13) . . . . ?
C1 C2 C3 C4 14.3(11) . . . . ?
C1 C2 C3 C5 143.8(12) . . . . ?
C1A N1A C4A O2A -173.6(9) . . . . ?
C1A N1A C4A C3A 3.5(11) . . . . ?
C1A C2A C3A C4A 3.6(11) . . . . ?
C1A C2A C3A C5A -117.4(13) . . . . ?
C2 C3 C5 C6 94.4(16) . . . . ?
C2 C3 C5 C10 -81.4(15) . . . . ?
C2A C3A C5A C10A -146.0(13) . . . . ?
C2A C3A C5A C6A 42.9(17) . . . . ?
C3 C5 C6 C7 -178.8(12) . . . . ?
C3 C5 C10 C9 179.2(13) . . . . ?
C3A C5A C10A C9A -177.4(11) . . . . ?
C3A C5A C6A C7A 177.0(11) . . . . ?
C5 C6 C7 C8 0(2) . . . . ?
C5A C10A C9A C8A 3(2) . . . . ?
C6 C5 C10 C9 3(2) . . . . ?
C6 C7 C8 C9 3(2) . . . . ?
C10A C5A C6A C7A 5.4(17) . . . . ?
C10A C9A C8A C7A 0.7(18) . . . . ?
C7 C8 C9 C10 -3(2) . . . . ?
C9A C8A C7A C6A -1(2) . . . . ?
C8 C9 C10 C5 0(2) . . . . ?
C8A C7A C6A C5A -2.1(19) . . . . ?
C10 C5 C6 C7 -3.1(19) . . . . ?
C6A C5A C10A C9A -6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_PII_298K
_database_code_depnum_ccdc_archive 'CCDC 1957490'
loop_
_audit_author_name
_audit_author_address
'Tatiana Timofeeva'
;New Mexico Highlands University
United States of America
;
_audit_update_record             
;
2019-10-03 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;
_audit_creation_date             2019-09-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        rac-3-phenylpyrrolidin-2,5-dione
_chemical_formula_moiety         'C10 H9 N O2'
_chemical_formula_sum            'C10 H9 N O2'
_chemical_formula_weight         175.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.57(4)
_cell_length_b                   5.719(15)
_cell_length_c                   20.69(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.77(2)
_cell_angle_gamma                90
_cell_volume                     1754(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    773
_cell_measurement_temperature    298
_cell_measurement_theta_max      18.427
_cell_measurement_theta_min      3.710
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7443
_exptl_absorpt_correction_T_min  0.5908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0692 before and 0.0442 after correction. The Ratio of minimum to maximum transmission is 0.7938. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.136
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4381
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        18.748
_diffrn_reflns_theta_max         18.748
_diffrn_reflns_theta_min         2.067
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                971
_reflns_number_total             1331
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         1331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0576P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0950
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C3A(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C2A(H2AA,H2AB)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N1A(H1A), C10(H10), C10A(H10A), C9(H9), C9A(H9A), C8(H8), C8A(H8A),
 C7(H7), C7A(H7A), C6(H6), C6A(H6A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5721(2) -0.1730(4) 0.55814(14) 0.0627(9) Uani 1 1 d . . . . .
O1A O 0.58691(17) 0.0202(5) 0.77220(14) 0.0583(8) Uani 1 1 d . . . . .
O2 O 0.34077(19) 0.1416(5) 0.61810(14) 0.0692(9) Uani 1 1 d . . . . .
O2A O 0.60888(15) -0.6403(5) 0.65675(14) 0.0583(8) Uani 1 1 d . . . . .
N1 N 0.4686(3) 0.0152(5) 0.59752(16) 0.0497(9) Uani 1 1 d . . . . .
H1 H 0.503395 0.126186 0.618352 0.060 Uiso 1 1 calc R . . . .
N1A N 0.58296(19) -0.3334(6) 0.71900(16) 0.0450(9) Uani 1 1 d . . . . .
H1A H 0.531291 -0.379150 0.721199 0.054 Uiso 1 1 calc R . . . .
C4 C 0.3809(3) -0.0031(8) 0.5963(2) 0.0512(12) Uani 1 1 d . . . . .
C4A C 0.6336(2) -0.4611(8) 0.6883(2) 0.0448(11) Uani 1 1 d . . . . .
C1 C 0.4967(3) -0.1568(7) 0.5630(2) 0.0489(11) Uani 1 1 d . . . . .
C1A C 0.6218(3) -0.1260(7) 0.7460(2) 0.0440(11) Uani 1 1 d . . . . .
C2 C 0.4180(2) -0.3107(6) 0.5320(2) 0.0575(12) Uani 1 1 d . . . . .
H2A H 0.433997 -0.473766 0.541502 0.069 Uiso 1 1 calc R . . . .
H2B H 0.396066 -0.288684 0.483191 0.069 Uiso 1 1 calc R . . . .
C2A C 0.7113(2) -0.1110(6) 0.7350(2) 0.0586(12) Uani 1 1 d . . . . .
H2AA H 0.758590 -0.094793 0.777888 0.070 Uiso 1 1 calc R . . . .
H2AB H 0.713647 0.022334 0.706576 0.070 Uiso 1 1 calc R . . . .
C3 C 0.3466(2) -0.2361(6) 0.5649(2) 0.0476(11) Uani 1 1 d . . . . .
H3 H 0.349788 -0.345540 0.601967 0.057 Uiso 1 1 calc R . . . .
C3A C 0.7228(2) -0.3393(6) 0.6998(2) 0.0460(11) Uani 1 1 d . . . . .
H3A H 0.730565 -0.302107 0.655659 0.055 Uiso 1 1 calc R . . . .
C5 C 0.2512(3) -0.2324(7) 0.5199(2) 0.0484(11) Uani 1 1 d . . . . .
C5A C 0.7990(2) -0.4941(6) 0.7386(2) 0.0399(10) Uani 1 1 d . . . . .
C10 C 0.1953(3) -0.4182(7) 0.5211(2) 0.0646(13) Uani 1 1 d . . . . .
H10 H 0.217419 -0.545241 0.549352 0.078 Uiso 1 1 calc R . . . .
C10A C 0.8491(2) -0.6120(7) 0.7047(2) 0.0484(11) Uani 1 1 d . . . . .
H10A H 0.836871 -0.589551 0.658257 0.058 Uiso 1 1 calc R . . . .
C9 C 0.1070(4) -0.4162(10) 0.4805(3) 0.0835(15) Uani 1 1 d . . . . .
H9 H 0.069966 -0.544064 0.480297 0.100 Uiso 1 1 calc R . . . .
C9A C 0.9169(3) -0.7622(7) 0.7381(3) 0.0626(12) Uani 1 1 d . . . . .
H9A H 0.949996 -0.840988 0.714281 0.075 Uiso 1 1 calc R . . . .
C8 C 0.0740(3) -0.2297(13) 0.4412(3) 0.0900(18) Uani 1 1 d . . . . .
H8 H 0.013325 -0.225454 0.415992 0.108 Uiso 1 1 calc R . . . .
C8A C 0.9355(3) -0.7952(7) 0.8056(3) 0.0632(13) Uani 1 1 d . . . . .
H8A H 0.981529 -0.896569 0.828240 0.076 Uiso 1 1 calc R . . . .
C7 C 0.1287(4) -0.0466(9) 0.4379(3) 0.0942(18) Uani 1 1 d . . . . .
H7 H 0.106112 0.078753 0.409125 0.113 Uiso 1 1 calc R . . . .
C7A C 0.8870(3) -0.6807(8) 0.8408(2) 0.0683(13) Uani 1 1 d . . . . .
H7A H 0.900476 -0.703085 0.887317 0.082 Uiso 1 1 calc R . . . .
C6 C 0.2171(3) -0.0487(7) 0.4773(2) 0.0722(14) Uani 1 1 d . . . . .
H6 H 0.254503 0.075974 0.475112 0.087 Uiso 1 1 calc R . . . .
C6A C 0.8178(3) -0.5313(7) 0.8072(3) 0.0573(12) Uani 1 1 d . . . . .
H6A H 0.784023 -0.455867 0.831044 0.069 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.213(5) . ?
O1A C1A 1.211(5) . ?
O2 C4 1.204(5) . ?
O2A C4A 1.213(5) . ?
N1 H1 0.8600 . ?
N1 C4 1.361(6) . ?
N1 C1 1.364(5) . ?
N1A H1A 0.8600 . ?
N1A C4A 1.365(5) . ?
N1A C1A 1.371(5) . ?
C4 C3 1.507(6) . ?
C4A C3A 1.505(6) . ?
C1 C2 1.485(6) . ?
C1A C2A 1.482(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.530(6) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A C3A 1.531(6) . ?
C3 H3 0.9800 . ?
C3 C5 1.492(6) . ?
C3A H3A 0.9800 . ?
C3A C5A 1.501(5) . ?
C5 C10 1.378(6) . ?
C5 C6 1.370(6) . ?
C5A C10A 1.375(5) . ?
C5A C6A 1.375(6) . ?
C10 H10 0.9300 . ?
C10 C9 1.375(6) . ?
C10A H10A 0.9300 . ?
C10A C9A 1.372(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.345(7) . ?
C9A H9A 0.9300 . ?
C9A C8A 1.350(7) . ?
C8 H8 0.9300 . ?
C8 C7 1.364(7) . ?
C8A H8A 0.9300 . ?
C8A C7A 1.365(6) . ?
C7 H7 0.9300 . ?
C7 C6 1.369(6) . ?
C7A H7A 0.9300 . ?
C7A C6A 1.384(6) . ?
C6 H6 0.9300 . ?
C6A H6A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 H1 122.8 . . ?
C4 N1 C1 114.5(4) . . ?
C1 N1 H1 122.8 . . ?
C4A N1A H1A 123.0 . . ?
C4A N1A C1A 114.0(4) . . ?
C1A N1A H1A 123.0 . . ?
O2 C4 N1 124.9(4) . . ?
O2 C4 C3 127.8(4) . . ?
N1 C4 C3 107.3(4) . . ?
O2A C4A N1A 124.7(4) . . ?
O2A C4A C3A 127.0(4) . . ?
N1A C4A C3A 108.3(4) . . ?
O1 C1 N1 124.9(4) . . ?
O1 C1 C2 127.6(4) . . ?
N1 C1 C2 107.4(4) . . ?
O1A C1A N1A 125.3(4) . . ?
O1A C1A C2A 126.9(4) . . ?
N1A C1A C2A 107.8(4) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C1 C2 C3 104.9(4) . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C1A C2A H2AA 110.5 . . ?
C1A C2A H2AB 110.5 . . ?
C1A C2A C3A 106.0(3) . . ?
H2AA C2A H2AB 108.7 . . ?
C3A C2A H2AA 110.5 . . ?
C3A C2A H2AB 110.5 . . ?
C4 C3 C2 103.2(3) . . ?
C4 C3 H3 107.5 . . ?
C2 C3 H3 107.5 . . ?
C5 C3 C4 114.2(3) . . ?
C5 C3 C2 116.5(4) . . ?
C5 C3 H3 107.5 . . ?
C4A C3A C2A 103.5(3) . . ?
C4A C3A H3A 108.9 . . ?
C2A C3A H3A 108.9 . . ?
C5A C3A C4A 110.6(3) . . ?
C5A C3A C2A 115.9(3) . . ?
C5A C3A H3A 108.9 . . ?
C10 C5 C3 119.4(4) . . ?
C6 C5 C3 121.9(4) . . ?
C6 C5 C10 118.7(4) . . ?
C10A C5A C3A 119.7(4) . . ?
C10A C5A C6A 118.3(4) . . ?
C6A C5A C3A 121.9(4) . . ?
C5 C10 H10 119.9 . . ?
C9 C10 C5 120.1(4) . . ?
C9 C10 H10 119.9 . . ?
C5A C10A H10A 119.3 . . ?
C9A C10A C5A 121.3(4) . . ?
C9A C10A H10A 119.3 . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.1(4) . . ?
C8 C9 H9 119.9 . . ?
C10A C9A H9A 120.1 . . ?
C8A C9A C10A 119.8(4) . . ?
C8A C9A H9A 120.1 . . ?
C9 C8 H8 119.7 . . ?
C9 C8 C7 120.7(5) . . ?
C7 C8 H8 119.7 . . ?
C9A C8A H8A 119.8 . . ?
C9A C8A C7A 120.4(4) . . ?
C7A C8A H8A 119.8 . . ?
C8 C7 H7 120.2 . . ?
C8 C7 C6 119.5(5) . . ?
C6 C7 H7 120.2 . . ?
C8A C7A H7A 120.0 . . ?
C8A C7A C6A 120.0(5) . . ?
C6A C7A H7A 120.0 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 H6 119.6 . . ?
C5A C6A C7A 120.1(4) . . ?
C5A C6A H6A 119.9 . . ?
C7A C6A H6A 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O1A 0.86 1.97 2.832(8) 178.8 2_646 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 170.3(4) . . . . ?
O1A C1A C2A C3A -179.5(4) . . . . ?
O2 C4 C3 C2 166.6(4) . . . . ?
O2 C4 C3 C5 39.2(6) . . . . ?
O2A C4A C3A C2A 173.5(4) . . . . ?
O2A C4A C3A C5A -61.8(5) . . . . ?
N1 C4 C3 C2 -14.9(4) . . . . ?
N1 C4 C3 C5 -142.4(4) . . . . ?
N1 C1 C2 C3 -11.4(4) . . . . ?
N1A C4A C3A C2A -5.8(4) . . . . ?
N1A C4A C3A C5A 118.9(4) . . . . ?
N1A C1A C2A C3A -1.7(4) . . . . ?
C4 N1 C1 O1 -179.7(3) . . . . ?
C4 N1 C1 C2 1.9(4) . . . . ?
C4 C3 C5 C10 -140.7(4) . . . . ?
C4 C3 C5 C6 39.2(5) . . . . ?
C4A N1A C1A O1A 175.7(4) . . . . ?
C4A N1A C1A C2A -2.2(4) . . . . ?
C4A C3A C5A C10A 101.2(4) . . . . ?
C4A C3A C5A C6A -75.6(4) . . . . ?
C1 N1 C4 O2 -172.8(4) . . . . ?
C1 N1 C4 C3 8.7(4) . . . . ?
C1 C2 C3 C4 15.7(4) . . . . ?
C1 C2 C3 C5 141.7(3) . . . . ?
C1A N1A C4A O2A -174.1(3) . . . . ?
C1A N1A C4A C3A 5.2(4) . . . . ?
C1A C2A C3A C4A 4.4(4) . . . . ?
C1A C2A C3A C5A -116.7(4) . . . . ?
C2 C3 C5 C10 99.0(4) . . . . ?
C2 C3 C5 C6 -81.1(5) . . . . ?
C2A C3A C5A C10A -141.5(3) . . . . ?
C2A C3A C5A C6A 41.7(5) . . . . ?
C3 C5 C10 C9 179.3(4) . . . . ?
C3 C5 C6 C7 -178.2(4) . . . . ?
C3A C5A C10A C9A -177.4(3) . . . . ?
C3A C5A C6A C7A 178.1(3) . . . . ?
C5 C10 C9 C8 -2.1(7) . . . . ?
C5A C10A C9A C8A -0.3(6) . . . . ?
C10 C5 C6 C7 1.7(6) . . . . ?
C10 C9 C8 C7 3.9(7) . . . . ?
C10A C5A C6A C7A 1.3(5) . . . . ?
C10A C9A C8A C7A 0.2(6) . . . . ?
C9 C8 C7 C6 -2.8(8) . . . . ?
C9A C8A C7A C6A 0.6(6) . . . . ?
C8 C7 C6 C5 0.0(7) . . . . ?
C8A C7A C6A C5A -1.3(6) . . . . ?
C6 C5 C10 C9 -0.6(6) . . . . ?
C6A C5A C10A C9A -0.5(5) . . . . ?

_olex2_exptl_crystal_mounting_method 'Single plate was mounted on nylon loop'
_olex2_submission_original_sample_id AVK14A
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_avk14a
_database_code_depnum_ccdc_archive 'CCDC 1888876'
loop_
_audit_author_name
_audit_author_address
'Boris Averkiev'
;New Mexico Highlands University
United States of America
;
_audit_update_record             
;
2019-01-08 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        3-phenylpyrrolidine-2,5-dione
_chemical_name_common            ?
_chemical_melting_point          353.2
_chemical_formula_moiety         'C10 H9 N O2'
_chemical_formula_sum            'C10 H9 N O2'
_chemical_formula_weight         175.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.564(5)
_cell_length_b                   5.7158(19)
_cell_length_c                   20.595(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.363(6)
_cell_angle_gamma                90
_cell_volume                     1748.6(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    215(2)
_cell_measurement_reflns_used    3776
_cell_measurement_theta_min      3.71
_cell_measurement_theta_max      25.38

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6544
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   
; 
Olex2 1.2 
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506) 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      215(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22399
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.072
_diffrn_reflns_theta_max         28.071
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4257
_reflns_number_gt                2869
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0398P)²+0.2610P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4257
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.60947(7) 0.13738(17) 0.15603(5) 0.0379(3) Uani 1 1 d . . . . .
O2A O 0.58707(7) -0.52514(19) 0.27223(5) 0.0375(3) Uani 1 1 d . . . . .
N1A N 0.58340(8) -0.1702(2) 0.21925(6) 0.0283(3) Uani 1 1 d . . . . .
H1A H 0.5310(11) -0.126(3) 0.2215(8) 0.034(4) Uiso 1 1 d . . . . .
C1A C 0.63389(9) -0.0423(2) 0.18786(7) 0.0272(3) Uani 1 1 d . . . . .
C2A C 0.72391(9) -0.1648(2) 0.19905(8) 0.0291(3) Uani 1 1 d . . . . .
H2A H 0.7303(10) -0.195(3) 0.1535(8) 0.030(4) Uiso 1 1 d . . . . .
C3A C 0.71235(11) -0.3931(3) 0.23419(11) 0.0399(4) Uani 1 1 d . . . . .
H3AA H 0.7570(13) -0.418(3) 0.2751(10) 0.055(6) Uiso 1 1 d . . . . .
H3AB H 0.7120(12) -0.526(3) 0.2053(9) 0.059(6) Uiso 1 1 d . . . . .
C4A C 0.62242(9) -0.3785(2) 0.24596(7) 0.0277(3) Uani 1 1 d . . . . .
C5A C 0.79995(9) -0.0061(2) 0.23811(7) 0.0261(3) Uani 1 1 d . . . . .
C6A C 0.85061(10) 0.1136(3) 0.20382(8) 0.0326(3) Uani 1 1 d . . . . .
H6A H 0.8379(11) 0.093(3) 0.1544(9) 0.044(5) Uiso 1 1 d . . . . .
C7A C 0.91872(11) 0.2651(3) 0.23834(9) 0.0409(4) Uani 1 1 d . . . . .
H7A H 0.9539(13) 0.344(3) 0.2131(9) 0.058(5) Uiso 1 1 d . . . . .
C8A C 0.93692(11) 0.2968(3) 0.30703(9) 0.0437(4) Uani 1 1 d . . . . .
H8A H 0.9855(13) 0.402(3) 0.3310(9) 0.055(5) Uiso 1 1 d . . . . .
C9A C 0.88729(11) 0.1792(3) 0.34165(9) 0.0454(4) Uani 1 1 d . . . . .
H9A H 0.9008(13) 0.202(4) 0.3911(11) 0.072(6) Uiso 1 1 d . . . . .
C10A C 0.81889(11) 0.0291(3) 0.30759(8) 0.0378(4) Uani 1 1 d . . . . .
H10A H 0.7813(11) -0.049(3) 0.3303(8) 0.044(5) Uiso 1 1 d . . . . .
O1B O 0.34038(8) 0.3536(2) 0.11826(6) 0.0463(3) Uani 1 1 d . . . . .
O2B O 0.57301(7) 0.6713(2) 0.05819(5) 0.0409(3) Uani 1 1 d . . . . .
N1B N 0.46956(9) 0.4810(2) 0.09824(6) 0.0328(3) Uani 1 1 d . . . . .
H1B H 0.5061(12) 0.361(3) 0.1193(9) 0.053(5) Uiso 1 1 d . . . . .
C1B C 0.38106(10) 0.4998(3) 0.09657(7) 0.0321(3) Uani 1 1 d . . . . .
C2B C 0.34684(10) 0.7360(3) 0.06516(8) 0.0328(3) Uani 1 1 d . . . . .
H2B H 0.3516(10) 0.839(3) 0.1020(8) 0.032(4) Uiso 1 1 d . . . . .
C3B C 0.41790(11) 0.8109(3) 0.03156(9) 0.0371(4) Uani 1 1 d . . . . .
H3BA H 0.4355(12) 0.973(3) 0.0376(8) 0.049(5) Uiso 1 1 d . . . . .
H3BB H 0.3985(11) 0.777(3) -0.0181(9) 0.049(5) Uiso 1 1 d . . . . .
C4B C 0.49745(10) 0.6557(3) 0.06281(7) 0.0318(3) Uani 1 1 d . . . . .
C5B C 0.25041(10) 0.7331(3) 0.02015(7) 0.0333(3) Uani 1 1 d . . . . .
C6B C 0.19471(11) 0.9210(3) 0.02108(9) 0.0423(4) Uani 1 1 d . . . . .
H6B H 0.2184(12) 1.049(3) 0.0511(9) 0.053(5) Uiso 1 1 d . . . . .
C7B C 0.10550(13) 0.9198(4) -0.01933(11) 0.0549(5) Uani 1 1 d . . . . .
H7B H 0.0679(14) 1.053(4) -0.0182(10) 0.064(6) Uiso 1 1 d . . . . .
C8B C 0.07177(13) 0.7301(4) -0.05988(11) 0.0602(6) Uani 1 1 d . . . . .
H8B H 0.0106(15) 0.728(3) -0.0867(11) 0.071(6) Uiso 1 1 d . . . . .
C9B C 0.12709(14) 0.5451(4) -0.06190(11) 0.0620(6) Uani 1 1 d . . . . .
H9B H 0.1053(15) 0.417(4) -0.0906(11) 0.076(7) Uiso 1 1 d . . . . .
C10B C 0.21650(13) 0.5462(3) -0.02267(9) 0.0491(5) Uani 1 1 d . . . . .
H10B H 0.2555(13) 0.413(4) -0.0253(9) 0.064(6) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C1A 1.2169(17) . ?
O2A C4A 1.2149(17) . ?
N1A C1A 1.3682(19) . ?
N1A C4A 1.3748(19) . ?
N1A H1A 0.868(17) . ?
C1A C2A 1.521(2) . ?
C2A C5A 1.517(2) . ?
C2A C3A 1.528(2) . ?
C2A H2A 0.988(15) . ?
C3A C4A 1.492(2) . ?
C3A H3AA 0.929(19) . ?
C3A H3AB 0.96(2) . ?
C5A C6A 1.386(2) . ?
C5A C10A 1.387(2) . ?
C6A C7A 1.389(2) . ?
C6A H6A 0.985(17) . ?
C7A C8A 1.369(3) . ?
C7A H7A 0.972(19) . ?
C8A C9A 1.373(3) . ?
C8A H8A 0.977(19) . ?
C9A C10A 1.384(2) . ?
C9A H9A 0.99(2) . ?
C10A H10A 0.960(17) . ?
O1B C1B 1.2114(18) . ?
O2B C4B 1.2110(18) . ?
N1B C1B 1.372(2) . ?
N1B C4B 1.381(2) . ?
N1B H1B 0.914(19) . ?
C1B C2B 1.523(2) . ?
C2B C5B 1.511(2) . ?
C2B C3B 1.530(2) . ?
C2B H2B 0.945(15) . ?
C3B C4B 1.503(2) . ?
C3B H3BA 0.963(18) . ?
C3B H3BB 0.996(18) . ?
C5B C6B 1.384(2) . ?
C5B C10B 1.385(2) . ?
C6B C7B 1.390(3) . ?
C6B H6B 0.956(19) . ?
C7B C8B 1.373(3) . ?
C7B H7B 0.97(2) . ?
C8B C9B 1.372(3) . ?
C8B H8B 0.95(2) . ?
C9B C10B 1.385(3) . ?
C9B H9B 0.94(2) . ?
C10B H10B 0.98(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A C4A 113.84(12) . . ?
C1A N1A H1A 123.5(10) . . ?
C4A N1A H1A 122.6(10) . . ?
O1A C1A N1A 125.05(13) . . ?
O1A C1A C2A 126.55(13) . . ?
N1A C1A C2A 108.40(12) . . ?
C5A C2A C1A 110.03(11) . . ?
C5A C2A C3A 116.27(13) . . ?
C1A C2A C3A 103.38(11) . . ?
C5A C2A H2A 108.9(8) . . ?
C1A C2A H2A 106.6(8) . . ?
C3A C2A H2A 111.1(9) . . ?
C4A C3A C2A 106.13(12) . . ?
C4A C3A H3AA 110.2(12) . . ?
C2A C3A H3AA 113.5(12) . . ?
C4A C3A H3AB 108.1(11) . . ?
C2A C3A H3AB 111.2(11) . . ?
H3AA C3A H3AB 107.6(16) . . ?
O2A C4A N1A 124.83(13) . . ?
O2A C4A C3A 127.25(14) . . ?
N1A C4A C3A 107.88(12) . . ?
C6A C5A C10A 118.43(14) . . ?
C6A C5A C2A 119.82(13) . . ?
C10A C5A C2A 121.72(13) . . ?
C5A C6A C7A 120.68(16) . . ?
C5A C6A H6A 119.8(10) . . ?
C7A C6A H6A 119.5(10) . . ?
C8A C7A C6A 120.15(16) . . ?
C8A C7A H7A 121.0(11) . . ?
C6A C7A H7A 118.8(11) . . ?
C7A C8A C9A 119.78(16) . . ?
C7A C8A H8A 119.7(10) . . ?
C9A C8A H8A 120.6(10) . . ?
C8A C9A C10A 120.47(17) . . ?
C8A C9A H9A 119.5(12) . . ?
C10A C9A H9A 120.1(12) . . ?
C9A C10A C5A 120.48(15) . . ?
C9A C10A H10A 121.9(10) . . ?
C5A C10A H10A 117.5(10) . . ?
C1B N1B C4B 113.70(13) . . ?
C1B N1B H1B 123.3(11) . . ?
C4B N1B H1B 123.0(11) . . ?
O1B C1B N1B 124.63(14) . . ?
O1B C1B C2B 127.82(14) . . ?
N1B C1B C2B 107.53(13) . . ?
C5B C2B C1B 114.08(13) . . ?
C5B C2B C3B 116.44(13) . . ?
C1B C2B C3B 103.39(13) . . ?
C5B C2B H2B 109.0(9) . . ?
C1B C2B H2B 106.1(9) . . ?
C3B C2B H2B 107.2(9) . . ?
C4B C3B C2B 104.81(13) . . ?
C4B C3B H3BA 110.3(10) . . ?
C2B C3B H3BA 115.2(10) . . ?
C4B C3B H3BB 106.4(10) . . ?
C2B C3B H3BB 111.8(10) . . ?
H3BA C3B H3BB 107.9(14) . . ?
O2B C4B N1B 124.11(14) . . ?
O2B C4B C3B 128.16(15) . . ?
N1B C4B C3B 107.72(13) . . ?
C6B C5B C10B 119.08(16) . . ?
C6B C5B C2B 119.63(15) . . ?
C10B C5B C2B 121.29(14) . . ?
C5B C6B C7B 120.37(19) . . ?
C5B C6B H6B 118.6(11) . . ?
C7B C6B H6B 121.0(11) . . ?
C8B C7B C6B 120.04(19) . . ?
C8B C7B H7B 120.9(12) . . ?
C6B C7B H7B 119.0(12) . . ?
C9B C8B C7B 119.83(19) . . ?
C9B C8B H8B 120.1(13) . . ?
C7B C8B H8B 120.0(13) . . ?
C8B C9B C10B 120.6(2) . . ?
C8B C9B H9B 120.6(13) . . ?
C10B C9B H9B 118.8(14) . . ?
C9B C10B C5B 120.04(19) . . ?
C9B C10B H10B 119.5(11) . . ?
C5B C10B H10B 120.4(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4A N1A C1A O1A 173.71(13) . . . . ?
C4A N1A C1A C2A -5.63(15) . . . . ?
O1A C1A C2A C5A 62.00(19) . . . . ?
N1A C1A C2A C5A -118.67(13) . . . . ?
O1A C1A C2A C3A -173.18(15) . . . . ?
N1A C1A C2A C3A 6.15(16) . . . . ?
C5A C2A C3A C4A 116.06(15) . . . . ?
C1A C2A C3A C4A -4.60(17) . . . . ?
C1A N1A C4A O2A -175.30(13) . . . . ?
C1A N1A C4A C3A 2.50(17) . . . . ?
C2A C3A C4A O2A 179.39(14) . . . . ?
C2A C3A C4A N1A 1.66(18) . . . . ?
C1A C2A C5A C6A -101.59(15) . . . . ?
C3A C2A C5A C6A 141.38(14) . . . . ?
C1A C2A C5A C10A 76.40(17) . . . . ?
C3A C2A C5A C10A -40.64(19) . . . . ?
C10A C5A C6A C7A 0.0(2) . . . . ?
C2A C5A C6A C7A 178.05(14) . . . . ?
C5A C6A C7A C8A 0.4(2) . . . . ?
C6A C7A C8A C9A -0.3(3) . . . . ?
C7A C8A C9A C10A -0.1(3) . . . . ?
C8A C9A C10A C5A 0.5(3) . . . . ?
C6A C5A C10A C9A -0.4(2) . . . . ?
C2A C5A C10A C9A -178.43(14) . . . . ?
C4B N1B C1B O1B 172.22(14) . . . . ?
C4B N1B C1B C2B -9.49(16) . . . . ?
O1B C1B C2B C5B -38.5(2) . . . . ?
N1B C1B C2B C5B 143.30(13) . . . . ?
O1B C1B C2B C3B -165.92(16) . . . . ?
N1B C1B C2B C3B 15.87(16) . . . . ?
C5B C2B C3B C4B -142.10(13) . . . . ?
C1B C2B C3B C4B -16.16(16) . . . . ?
C1B N1B C4B O2B 179.75(14) . . . . ?
C1B N1B C4B C3B -1.41(17) . . . . ?
C2B C3B C4B O2B -169.73(15) . . . . ?
C2B C3B C4B N1B 11.49(16) . . . . ?
C1B C2B C5B C6B 141.55(15) . . . . ?
C3B C2B C5B C6B -98.08(18) . . . . ?
C1B C2B C5B C10B -39.0(2) . . . . ?
C3B C2B C5B C10B 81.42(19) . . . . ?
C10B C5B C6B C7B 1.4(2) . . . . ?
C2B C5B C6B C7B -179.14(15) . . . . ?
C5B C6B C7B C8B 0.8(3) . . . . ?
C6B C7B C8B C9B -1.9(3) . . . . ?
C7B C8B C9B C10B 0.9(3) . . . . ?
C8B C9B C10B C5B 1.3(3) . . . . ?
C6B C5B C10B C9B -2.4(3) . . . . ?
C2B C5B C10B C9B 178.10(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1A O2A 0.868(17) 1.967(17) 2.8346(18) 179.4(16) 2_655
N1B H1B O1A 0.914(19) 2.017(19) 2.9102(18) 165.4(16) .

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.036


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexanes/acetone (2:1)'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_PII_175K
_database_code_depnum_ccdc_archive 'CCDC 1957489'
loop_
_audit_author_name
_audit_author_address
'Tatiana Timofeeva'
;New Mexico Highlands University
United States of America
;
_audit_update_record             
;
2019-10-03 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;
_audit_creation_date             2019-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        rac-3-phenylpyrrolidin-2,5-dione
_chemical_formula_moiety         'C10 H9 N O2'
_chemical_formula_sum            'C10 H9 N O2'
_chemical_formula_weight         175.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.575(6)
_cell_length_b                   5.711(2)
_cell_length_c                   20.567(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.533(5)
_cell_angle_gamma                90
_cell_volume                     1744.5(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3740
_cell_measurement_temperature    175
_cell_measurement_theta_max      23.852
_cell_measurement_theta_min      3.716
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_correction_T_min  0.6463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0642 before and 0.0470 after correction. The Ratio of minimum to maximum transmission is 0.8675. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15783
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.116
_diffrn_reflns_theta_max         24.116
_diffrn_reflns_theta_min         2.743
_diffrn_ambient_temperature      175
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2158
_reflns_number_total             2756
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         2756
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+0.2338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0850
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C3A(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C2A(H2AA,H2AB)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C6A(H6A), C7A(H7A), C8A(H8A),
 C9A(H9A), C10A(H10A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.57284(7) 0.6714(2) 0.05841(5) 0.0413(3) Uani 1 1 d . . . . .
O2 O 0.34015(8) 0.3537(2) 0.11813(6) 0.0466(3) Uani 1 1 d . . . . .
N1 N 0.46906(9) 0.4815(2) 0.09822(6) 0.0326(3) Uani 1 1 d . . . . .
C1 C 0.49715(11) 0.6555(3) 0.06282(7) 0.0319(4) Uani 1 1 d . . . . .
C2 C 0.41782(10) 0.8103(3) 0.03121(8) 0.0378(4) Uani 1 1 d . . . . .
H2A H 0.395418 0.786386 -0.018750 0.045 Uiso 1 1 calc R . . . .
H2B H 0.434032 0.977260 0.040517 0.045 Uiso 1 1 calc R . . . .
C3 C 0.34666(10) 0.7361(3) 0.06503(8) 0.0354(4) Uani 1 1 d . . . . .
H3 H 0.350275 0.847652 0.103235 0.042 Uiso 1 1 calc R . . . .
C4 C 0.38073(11) 0.4998(3) 0.09636(7) 0.0329(4) Uani 1 1 d . . . . .
C5 C 0.25033(10) 0.7329(3) 0.01977(8) 0.0338(4) Uani 1 1 d . . . . .
C6 C 0.19465(11) 0.9211(3) 0.02099(9) 0.0435(4) Uani 1 1 d . . . . .
H6 H 0.217630 1.051313 0.049684 0.052 Uiso 1 1 calc R . . . .
C7 C 0.10541(12) 0.9201(4) -0.01955(10) 0.0547(5) Uani 1 1 d . . . . .
H7 H 0.067816 1.050916 -0.019324 0.066 Uiso 1 1 calc R . . . .
C8 C 0.07168(13) 0.7301(4) -0.05987(10) 0.0598(6) Uani 1 1 d . . . . .
H8 H 0.010024 0.726517 -0.086197 0.072 Uiso 1 1 calc R . . . .
C9 C 0.12704(14) 0.5446(4) -0.06226(10) 0.0625(6) Uani 1 1 d . . . . .
H9 H 0.103912 0.414811 -0.091085 0.075 Uiso 1 1 calc R . . . .
C10 C 0.21585(13) 0.5470(3) -0.02295(9) 0.0502(5) Uani 1 1 d . . . . .
H10 H 0.253855 0.419120 -0.025241 0.060 Uiso 1 1 calc R . . . .
O1A O 0.58702(7) -0.52561(19) 0.27233(5) 0.0376(3) Uani 1 1 d . . . . .
O2A O 0.60940(7) 0.13790(18) 0.15604(5) 0.0382(3) Uani 1 1 d . . . . .
N1A N 0.58338(9) -0.1702(2) 0.21925(6) 0.0291(3) Uani 1 1 d . . . . .
C1A C 0.62243(10) -0.3788(3) 0.24607(7) 0.0289(4) Uani 1 1 d . . . . .
C2A C 0.71242(10) -0.3935(3) 0.23465(10) 0.0397(4) Uani 1 1 d . . . . .
H2AA H 0.714988 -0.529591 0.205493 0.048 Uiso 1 1 calc R . . . .
H2AB H 0.760574 -0.409960 0.278602 0.048 Uiso 1 1 calc R . . . .
C3A C 0.72379(9) -0.1642(2) 0.19920(8) 0.0297(4) Uani 1 1 d . . . . .
H3A H 0.731755 -0.201726 0.153881 0.036 Uiso 1 1 calc R . . . .
C4A C 0.63395(10) -0.0423(3) 0.18797(7) 0.0280(3) Uani 1 1 d . . . . .
C5A C 0.79992(9) -0.0063(2) 0.23819(7) 0.0274(3) Uani 1 1 d . . . . .
C6A C 0.81875(11) 0.0297(3) 0.30767(8) 0.0387(4) Uani 1 1 d . . . . .
H6A H 0.784525 -0.049386 0.332112 0.046 Uiso 1 1 calc R . . . .
C7A C 0.88712(11) 0.1803(3) 0.34168(9) 0.0451(4) Uani 1 1 d . . . . .
H7A H 0.899736 0.202886 0.389401 0.054 Uiso 1 1 calc R . . . .
C8A C 0.93685(11) 0.2974(3) 0.30722(9) 0.0432(4) Uani 1 1 d . . . . .
H8A H 0.983661 0.400574 0.330904 0.052 Uiso 1 1 calc R . . . .
C9A C 0.91859(11) 0.2645(3) 0.23844(9) 0.0412(4) Uani 1 1 d . . . . .
H9A H 0.952856 0.345340 0.214371 0.049 Uiso 1 1 calc R . . . .
C10A C 0.85046(10) 0.1140(3) 0.20378(8) 0.0334(4) Uani 1 1 d . . . . .
H10A H 0.838183 0.092865 0.156024 0.040 Uiso 1 1 calc R . . . .
H1A H 0.5319(12) -0.126(3) 0.2225(8) 0.044(5) Uiso 1 1 d . . . . .
H1 H 0.5039(12) 0.366(3) 0.1178(8) 0.043(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2126(19) . ?
O2 C4 1.2110(19) . ?
N1 C1 1.379(2) . ?
N1 C4 1.369(2) . ?
C1 C2 1.499(2) . ?
C2 C3 1.535(2) . ?
C3 C4 1.521(2) . ?
C3 C5 1.509(2) . ?
C5 C6 1.386(2) . ?
C5 C10 1.380(2) . ?
C6 C7 1.389(3) . ?
C7 C8 1.371(3) . ?
C8 C9 1.376(3) . ?
C9 C10 1.376(3) . ?
O1A C1A 1.2159(18) . ?
O2A C4A 1.2190(18) . ?
N1A C1A 1.375(2) . ?
N1A C4A 1.369(2) . ?
C1A C2A 1.492(2) . ?
C2A C3A 1.535(2) . ?
C3A C4A 1.517(2) . ?
C3A C5A 1.513(2) . ?
C5A C6A 1.385(2) . ?
C5A C10A 1.389(2) . ?
C6A C7A 1.384(2) . ?
C7A C8A 1.371(2) . ?
C8A C9A 1.369(2) . ?
C9A C10A 1.384(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C1 113.98(14) . . ?
O1 C1 N1 124.32(14) . . ?
O1 C1 C2 128.03(15) . . ?
N1 C1 C2 107.64(14) . . ?
C1 C2 C3 104.70(13) . . ?
C4 C3 C2 103.28(13) . . ?
C5 C3 C2 116.31(13) . . ?
C5 C3 C4 113.96(13) . . ?
O2 C4 N1 124.70(15) . . ?
O2 C4 C3 127.86(15) . . ?
N1 C4 C3 107.40(14) . . ?
C6 C5 C3 119.40(15) . . ?
C10 C5 C3 121.73(15) . . ?
C10 C5 C6 118.87(16) . . ?
C5 C6 C7 120.31(18) . . ?
C8 C7 C6 119.88(19) . . ?
C7 C8 C9 120.06(18) . . ?
C10 C9 C8 120.09(19) . . ?
C9 C10 C5 120.73(18) . . ?
C4A N1A C1A 113.77(13) . . ?
O1A C1A N1A 124.78(14) . . ?
O1A C1A C2A 127.21(14) . . ?
N1A C1A C2A 107.97(13) . . ?
C1A C2A C3A 105.98(12) . . ?
C4A C3A C2A 103.34(12) . . ?
C5A C3A C2A 116.16(13) . . ?
C5A C3A C4A 110.31(12) . . ?
O2A C4A N1A 124.92(14) . . ?
O2A C4A C3A 126.49(14) . . ?
N1A C4A C3A 108.59(13) . . ?
C6A C5A C3A 121.60(13) . . ?
C6A C5A C10A 118.43(14) . . ?
C10A C5A C3A 119.92(14) . . ?
C7A C6A C5A 120.37(15) . . ?
C8A C7A C6A 120.69(16) . . ?
C9A C8A C7A 119.56(16) . . ?
C8A C9A C10A 120.37(15) . . ?
C9A C10A C5A 120.58(15) . . ?

_olex2_submission_original_sample_id AVK14F3
_olex2_submission_special_instructions 'No special instructions were received'
